HCID 136340678, compound → HCID 136078935, compound

HRID 529275Notes

Reaction equation

HRID 529275 reaction equation
[N:1]([C@:4]1([CH2:43][OH:44])[O:8][C@@H:7]([N:9]2[C:40]3[N:39]=[C:16]([NH:17]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC(OC)=CC=4)[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[C@H:6]([F:41])[C@@H:5]1[OH:42])=[N+:2]=[N-:3]>C(O)=O>[N:1]([C@:4]1([CH2:43][OH:44])[O:8][C@@H:7]([N:9]2[C:40]3[N:39]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[C@H:6]([F:41])[C@@H:5]1[OH:42])=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 136340678HCID 136340678, compound

Product 1

HCID 136078935HCID 136078935, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Compound (27)—A solution of compound 50-8 (580 mg, 0.72 mmol) in 7N NH3 in CH3OH (30 mL) was stirred at R.T. overnight. The solvent was evaporated in vacuo, and the residue was purified on silica gel column using DCM/MeOH (95:5 to 90:10) to give 4′-azido-2′-fluoro-N2-(4-methoxytrityl)-2′-deoxyguanosine (332 mg, 77%). 4′-Azido-2′-fluoro-N2-(4-methoxytrityl)-2′-deoxyguanosine (80 mg, 0.13 mmol) was dissolved in 80% HCOOH (3 mL), stirred at R.T. for 3 hours. The solvent was evaporated at R.T. and co-evaporated with MeOH/toluene (3 times). Purification using RP-HPLC (water: acetonitrile) gave (27) (26.0 mg, 61%) as a white foam after lyophilization. 1H NMR (DMSO-d6) δ 3.55-3.67 (m, 2H), 4.69-4.77 (m, 1H), 5.37 (dd, J=2.4, 4.8 Hz, 1H), 5.51 (t, J=2.8 Hz, 1H), 5.65 (t, J=6.0 Hz, 1H), 6.13 (d, J=7.6 Hz, 1H), 6.30 (dd, J=2.4, 18.4 Hz, 1H), 6.60 (br s, 1H), 7.91 (s, 1H), 10.74 (br s, 1H); 19F NMR δ (−199.0 to −199.25, m); ESI-LCMS m/z=325.3 [M+H]+.

Workup

  1. customThe solvent was evaporated at R.T. and co-evaporated with MeOH/toluene (3 times)
  2. customPurification

Sources & evidence

ORD record
ord-a0843f0dc9a44959891ecf2c7f5792d5
Source dataset
uspto-grants-2016_05
Patent number
US09346848B2

Reaction notes

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